Cheap Flights From Chicago (September 28)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Miami, Florida Check Dates |
$183 Save 55% |
Oct 2026 – Aug 2027 | American Airlines |
|
Aspen, Colorado Check Dates |
$413 Save 31% |
Dec 2026 – Apr 2027 | United Airlines |
|
Athens, Greece Check Dates |
$570 Save 44% |
Jan 2027 – Feb 2027 | American Airlines |
|
Paris, France Check Dates |
$586 Save 43% |
Oct 2026 – Jan 2027 | TAP Portugal |
|
Rome, Italy Check Dates |
$627 Save 43% |
Oct 2026 – May 2027 | TAP Portugal |
|
Nha Trang, Vietnam Check Dates |
$1,079 Save 41% |
Nov 2026 | Delta |
Note: Flight prices can change in the matter of minutes. On average we see these deals last 2-3 days.
âš¡ How to Book
- Click the “Check Dates” button above.
- On Google Flights, click the Calendar icon to view the cheapest months.
- Select your specific dates and book directly with the airline.